Brain abscess is a life-threatening infection that can occur secondary to contiguous or hematogenous spread. Several underlying conditions can lead to brain abscesses, such as dental infection, otitis media, sinusitis, and immunosuppression. Esophageal perforation leading to brain abscesses is extremely rare. We report a rare case of a 32-year-old man who presented to the emergency department with progressive headaches and upper-extremity weakness. Upon further evaluation, computed tomography (CT) revealed multiple brain abscesses secondary to Streptococcus intermedius infection. The patient eventually underwent esophagogastroduodenoscopy (EGD), which showed a perforation in the middle third of the esophagus. This case highlights the importance of considering esophageal perforation as a predisposing condition for brain abscesses.